Phenylsemioxamazide insecticidal compositions



Patented May 17, 1949' I 2,470,160

UNITED STATES PATENT OFFICE- PHENYLSEMIOXAMAZIDE INSECTICIDAL COMPOSITIONS Samuel I. Gertler, Washington, D. 0., assignor to the United States of America as represented by the Secretary of Agriculture No Drawing. Application July 19, 1946,

Serial No. 684,916

13 Claims. (Cl. 167--30) (Granted under the act of March 3, 1883, as amended April 30, 1928:3711 0. G. 757) This application is made under the act of compound in question with the other ingredients March 3, 1883, as amended by the act of April as mentioned above. A spray composition will 30. 1928, and the invention herein described, if denote a certain number of pounds of compound patented, may be manufactured and used by or plus a wetting agent in 100 gallons of water or for the Government of the United States of pounds of composition plus other dust plus wet- America for governmental purposes without the ting agent in 100 gallons of water. payment to me of any royalty thereon. EXAMPLE 1 This invention relates to improvements in materials for destroying or checking. the growth l-phenlllsemioxamazide or multiplication of living organisms whether H H plant or animal which are economically injurious 1, l to man. A:

.An object of the invention is to provide insec- 0: tlcidal compositions for dusting or spraying del- A spray composition, containing 2 pounds of 1- icate vegetation such as bean plants, peach trees, phenylsemioxamazide in 100 gallons of water, and plants grown under glass, without injury to when sprayed on cauliflower leaves which were foliage. exposed to newly hatched larvae of the European A further object of the invention is to provide corn borer gave 100 percent kill in 48 hours.. A

insecticidal compositions which are relatively similar composition containing 1 pound per 100 nontoxic to man and domestic animals when gallons gave 96.9 percent kill in the same time.

taken by mouth, and which can be used in place A dust composition containing approximately of lead arsenate and other arsenicals for destroyequal parts of this compound and pyrophyllite, ing insects without leaving harmful residues on when dusted on pumpkin leaves and fed to the fruits and vegetables. fourth instar of the melonworm, gave a mortality Other objects will be apparent from the follow- 35 of 100 percent in 3 days. The same mixture made ing description of the invention. up into a spray composition at a concentration I have found that phenylsemioxamazides, which of 8 pounds to 100 gallons of water and sprayed may be designated by the following general foron pumpkin leaves fed to the same insect also mula gave 100 percent mortality in 3 days.

H H The above dust composition dusted on pigweed l l leaves and fed to the fourth instar of the Southern armyworm gave 100 percent kill in 3 days. =CNR When used as a spray composition as above, 87

percent kill was obtained in 3.days. The same dust composition dusted on pigweed leaves exposed to the fourth instar of the South- 1 m Wh ch R is selected from the group conslstmg ern beet webwor'm gave 100 percent kill in 3 days.

of hydrogen and an aliphatic radical of not more Th 1 th It than two carbon atoms, when incorporated in a 8 Spray composl Ion so gave 6 Same resu carrier to form a dust or spray composition, and k as such applied to material liable to attack by 40 h lampblac and Suspgnded m a insects. has a specific toxic efiect'upon such Suitable hquld p benzol f to the insects. The carrier forming the dust composi wounds of domestic animalsinfested with newly hatched larvae of the screwworm, gave complete tion with one of these compounds comprises a suitable material such as pyrophyllite or kaolin, with a sticking agent like glue, casein, rosin and control at a, concentration as low as 0.1 percent of the compound.

so forth. The carrier forming a spray composi- EXAMPLE 2 tion comprises a mixture of a suitable material such as pyrophyllite or kaolin, a wetting agent 5 methyl 1 phenyzsemioaf'ammde such as saponin, sodium lauryl sulfate, soap, and so forth, and water, the function of the wetting o=o-N-N- agent being to form a suspension ofthe composition in water, when so used.

In the following examples, which are illustra- H tive of the'invention. a dust composition will be A spray composition containing 4 pounds of 5- understood to mean a given concentration of the methyl-1-phenylsemioxamazide in gallons of A smear composition prepared by mixing the '3 water when sprayed on cauliflower leaves and fed to newly hatched larvae of the European corn borer, gave 100 percent kill in 48 hours. At a concentration of 1 pound in 100 gallons of water 96.0 percent kill was obtained in the same time. A dust composition containing approximately equal parts of this compound and pyrophyllite, when dusted on pumpkin leaves and fed to the fourth instar melonworm, gave 100 percent mortality in three days. A spray composition containing 8 pounds of the mixture in 100 gallons of water also gave 100 percent mortality in the same time.

The same dust composition, dusted on pig'weed leaves which were fed to the fourth instar of the Southern beet webworm gave a mortality of 100- percent in three days. The above spray composition, when sprayed on Swiss chard leaves fed to the same insect also gave 100 percent kill in three days.

The same dust composition, dusted on pigweed leaves and fed to the fourth instar Southern armyworm gave a mortality of 94 percent in 3 days.

A smear composition prepared as described in Example 1 and applied to newly hatched larvae of the screwworm gave complete control at a concentration as low as 0.05 percent.

100 gallons of water also gave 100 percent kill in the same period of time. I

The same dust composition applied to pigweed leaves and fed to the fourth instar of the Southern beet webworm gave a mortality of 100 percent in 3 days.

A smear composition prepared as described in Example 1 and applied to newly hatched larvae of the screwworm gave complete control at a concentration as low as 0.17 percent.

Foliage tests.A spray composition of each of the above examples preparedwith 8 pounds of compound and /8 pound of saponin per 100 galions of water, was sprayed on pumpkin, tomato,

collard, pea, bean, and radish plants to determine whether any injury to the foliage could be noted. Practically no injury to any of these plants was caused by the above compositions.

It is to be understood that compositions containing the above mentioned compounds are merely used as examples and that this invention is not restricted to such use. Also the above examples are not to be construed as limiting either the method of application of these novel insecticides or the kinds of insects to which they may be applied. Compositions containing other members of this series of compounds have been found to show varying degrees of toxicity to different insects. For the control of certain types of insects it may be advantageous to admix any compound or composition of this class with known insecticides such as lead arsenate, derris, nicotine, pyrethrum, DDT, and soforth.

4 Having thus described my invention. I claim: -1. An insecticidal composition comprising a compound of the general formula in which R is selected from the group consisting of hydrogen and an aliphatic radical of not more than two carbon atoms.

3. An insecticidal composition comprising water, pyrophyllite, a wetting agent, and a compound of the general formula in which R is selected from the group consisting of hydrogen and an aliphatic radical of not more than two carbon atoms.

4. An insecticidal composition comprisin Pilrophyllite, a sticking agent and l-phenylsemioxamazide.

5. An insecticidal composition comprising water, pyrophyllite, a wetting agent and l-phenylsemioxamazide.

6. An. insecticidal composition comprising water, pyrophyllite, a wetting agent and 5- methyl-1-phenylsemioxamazide.

'7. An insecticidal composition comprising water, pyrophyllite, a wetting agent and 5- ethyl-l-phenylsemioxamazide.

8. An insecticidal composition comprising a dust carrier, sticking agent, and an insecticidally active ingredient of the formula 0= -N-N O=C-IITR in which R is selected from the group consisting of hydrogen and an aliphatic radical of not more than two carbon atoms, the carrier being present in an amount at least equal in weight to the said active ingredient.

9. An insecticidal composition comprising a dust, water, and a compound of the formula in which R is selected from the group consisting of hydrogen and an aliphatic radical of not more than two carbon atoms.

. 10. The composition defined in claim 9 in which the compound of the said formula is present in an amount no more than about equal in weight to the dust.

6 11. An insecticidal composition comprising: a 13. An insecticidal composition comprising compound of the formula: lampblack, benzol, and an insecticidal ingredient E H of the formula: O=C-NN- 3 v n H' in which R is selected from the group consisting a of hydrogen and an aliphatic radical of not more in which R 15 taken from the group consisting than two carbon atom nd a ri comprising of hydrogen and an aliphatic radical of not more water containing a. wetting agent to form a sus- 1 than two atomspension of the composition in water, the water SAMUEL ERTLER. being present in the ratio of 100 gallons of water to no more than about 4 pounds of the compound REFERENCES CITED of said formula. v r I The following references are of record in the 12. An insecticidal composition comprising: a 15 file of this patent: 9 the m'z UNITED STATES PATENTS o=c N-NC Number Name Date Y 2,272,047 Freeman Feb. 3, 1942 H OTHER REFERENCES in which R is selected from the group consisting oih drogen and an all hatic radical of not more Bulowz Berichte: volume page 3687- g two carbon a dust carrier; and a stracted 1n Beilstem, Band XV, page 265. (Copy wetting agent. of Berichte in Library.) 

